With Tried & True, our editors will give you an inside look at the pieces they simply cannot live without. Loeffler Randall Indy Espresso Tall Boot $695 at Loeffler RandallTo start, the pull-on boot has a 1.5 inch heel, which makes them both ultra-comfortable and walkable, while still giving a bit of support. And that elegant, not-rounded-not-square toe keeps the Indy from looking to dated to a specific year or trend cycle. Now, I own the Indy in the rich espresso, which in my opinion is the perfect color for fall. If there's only one pair of boots to expand the possibilities in your wardrobe, it's the Indy.